The present invention relates to a class of ortho-alkyl- and ortho-alkenyl-substituted benzenesulfonamides which are useful as general or selective pre-emergent or post-emergent herbicides and plant growth regulants.
U.S. Pat. No. 4,368,069 discloses and claims a class of herbicidal sulfonamides including compounds of the following structure: ##STR1## wherein R is ##STR2## R.sub.2 can be C.sub.2 -C.sub.5 alkenyl; n is 0 or 1;
R.sub.1 can be H; PA1 X and Y can be various substituents including CH.sub.3 or OCH.sub.3 ; and PA1 Z can be CH or N. PA1 R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA1 R.sub.3 is H or CH.sub.3 ; PA1 R.sub.4 is H, F, Cl, Br or CH.sub.3 ; PA1 R.sub.5 is F, Cl, Br, OC(O)R.sub.6, OC(O)CF.sub.3, OH, OCH.sub.2 .phi., OSO.sub.2 R.sub.6, OSO.sub.2 CF.sub.3, OSO.sub.2 C.sub.6 H.sub.5 R.sub.7, S(O).sub.m R.sub.6, OSO.sub.2 N(CH.sub.3).sub.2 or CO.sub.2 R.sub.8 ; PA1 R.sub.6 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.7 is H, F, Cl, Br, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA1 R.sub.8 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl; PA1 R.sub.9 is OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 R.sub.10 is H, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 R.sub.11 is H, Cl or OCH.sub.3 ; PA1 R.sub.12 is H or CH.sub.3 ; PA1 n is 0 or 1; PA1 m is 0, 1 or 2; PA1 A is ##STR6## X is CH.sub.3, OCH.sub.3, Cl, F, Br, CH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.2 H; PA1 Y is H, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of (a) F, (b) Cl or (c) Br, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2, CH(OCH.sub.2 CH.sub.3).sub.2, ##STR7## OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CH.sub.2 Cl, OCH.sub.2 CH.sub.2 Br or GCF.sub.2 T; wherein G is O or S and T is H, CHClF, CHBrF, CF.sub.2 H or CHFCF.sub.3 ; PA1 Z is CH, N, CCH.sub.3, CBr, CCl, CF or CCH.sub.2 CH.sub.3 ; PA1 X.sub.1 is O or CH.sub.2 ; PA1 Y.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl; PA1 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA1 Y.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; and PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 (a) when R.sub.4 is halogen, R.sub.5 is the same halogen; PA1 (b) when R.sub.5 is halogen, R.sub.4 is either hydrogen or the same halogen; PA1 (c) when n is 1, R.sub.11 is hydrogen; PA1 (d) when R.sub.12 is CH.sub.3 and R.sub.10 is alkoxy, R.sub.9 is the same alkoxy; and PA1 (e) when X is Cl, then Z is CH and Y is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3, OCH.sub.3, or OCF.sub.2 H. PA1 (1) Compounds of generic Formula I wherein R.sub.2 is H and R.sub.1 is (CH.sub.2).sub.n CH.sub.2 CHR.sub.4 R.sub.5, ##STR8## (2) Compounds of Preferred 1 wherein A is A-1; Z is CH or N; X is CH.sub.3, OCH.sub.3, Cl or OCF.sub.2 H and Y is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCF.sub.2 H, SCF.sub.2 H, CH.sub.2 OCH.sub.3 or CF.sub.3. PA1 (3) Compounds of Preferred 2 wherein R.sub.1 is CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 OH, ##STR9## (4) Compounds of Preferred 3 wherein R.sub.3 is H. PA1 R.sub.4 is H or CH.sub.3. PA1 R.sub.4 is H or CH.sub.3. ##STR18## wherein R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA1 R.sub.9 is OCH.sub.3 or OC.sub.2 H.sub.5 ; and PA1 R.sub.12 is H or CH.sub.3. ##STR19## wherein R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.5 is OC(O)R.sub.6, OC(O)CF.sub.3, OSO.sub.2 R.sub.6, OSO.sub.2 CF.sub.3, OSO.sub.2 C.sub.6 H.sub.4 R.sub.7, OCH.sub.2 Ph or OSO.sub.2 N(CH.sub.3).sub.2 ; and PA1 R.sub.6 and R.sub.7 are as previously defined. ##STR20## wherein R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA1 R.sub.4 is H or CH.sub.3 ; and PA1 R.sub.5 is F, Cl or Br. ##STR21## wherein R.sub.2 is as previously defined; PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.5 is OH, F, Cl, Br, OC(O)R.sub.6, OC(O)CF.sub.3, OSO.sub.2 R.sub.6, OSO.sub.2 CF.sub.3, OSO.sub.2 C.sub.6 H.sub.4 R.sub.7, OCH.sub.2 PH or OSO.sub.2 N(CH.sub.3).sub.2 ; and PA1 R.sub.6 and R.sub.7 are as previously defined. ##STR22## wherein R.sub.2, R.sub.9, R.sub.12, and n are as defined in the Summany of the Invention PA1 W. E. Truce and M. F. Amos, J. Am. Chem. Soc., 73, 3013 (1951) PA1 S. J. Shafer and W. D. Clossen, J. Org. Chem., 40, 889 (1975) PA1 D. Hellwinkel and M. Supp, Tetrahedron Lett., 1499 (1975) PA1 H. W. Gschwend and H. R. Rodriquez, Organic Reactions, 26, 1 (1979). PA1 R.sub.4 is H or CH.sub.3 ; and PA1 n is 0 or 1. PA1 R.sub.10 is OCH.sub.3 or OC.sub.2 H.sub.5. PA1 R.sub.10 is OCH.sub.3 or OC.sub.2 H.sub.5. PA1 R.sub.11 is Cl. PA1 R.sub.11 is OCH.sub.3. PA1 R.sub.11 is Cl. PA1 R.sub.11 is OCH.sub.3. PA1 n is 1. PA1 R.sub.2 and n are as previously defined. PA1 R.sub.4 =R.sub.5 =F, Cl, or Br. PA1 R.sub.4 is H or CH.sub.3. PA1 R.sub.4 is H or CH.sub.3. PA1 R.sub.4 is H or CH.sub.3 ; and PA1 R.sub.8 is C.sub.2 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl. PA1 R.sub.4 is H or CH.sub.3. PA1 R.sub.4 is H or CH.sub.3. PA1 Y is CH(OCH.sub.3).sub.2 or ##STR56## PA1 Y is CH(OCH.sub.3).sub.2 or ##STR58## PA1 Z is CH or N. PA1 R.sub.3 is CH.sub.3.
European Patent Application No. 81303176.2 (Publication Number 0 044 209) discloses and claims a large number of o-benzyl-substituted sulfonamides including the following: ##STR3## These compounds are useful as plant growth regulants and as herbicides.